It's not hard to make arguments for any of those guys, but just at a glance at the preseason player rankings (from September 2019) ESPN/Bleacher Report/SI all had Holiday as the better player. Those three publications had Smart at 87/54/82, Hayward at 65/43/59 and Holiday at 31/25/25. I'm not sure anything happened this season would change those rankings enough to put Holiday behind Hayward/Smart.
Due to age and contract I want no part of trading away Smart, but moving Hayward to preserve the salary slot would be a pretty nice move. The only negative in Holiday's game has been durability, but it's not like Hayward/Smart are much better in that regard. Holiday is a plus scorer, distributer and rebounder (for his size), and borderline all-nba defender. He's the kind of guy who would be a good fit on just about any team in the league, and when him and Marcus are on the court at the same time it's likely the best defensive backcourt combo in the league, while still doing lots of other things.
I will say Smart made clear this year he was undervalued, but my response to that in general is....
WHAT IN THE WORLD IS WITH THOSE HOLIDAY RANKS?
I guess just an overvaluation of his on-ball defense, and the "ooh 20 ppg" bump?
He was coming off a pretty decent season... 67 games (dude can't stay healthy), 21/5/7.7 is a nice line, but it came on .472/.325/.768 shooting, a significant drop in defensive contribution and what looks like a career outlier FTr.
Now don't get me wrong, that's a really good player.... it's not a top 25 in the league player. I guess maybe some people were for some reason projecting that at 29 his offense would stay or increase and his D would return to previous levels? (Neither happened, his defense remained below his peak by a good amount, probably in part due to not having AD behind him, and his offense slid a bit).
Listen, all the picks for Jrue is probably a slight overpay, but not awful. Anything beyond the 3 picks and S&T Hayward is not somethng we should be interested in.
I also have concerns that it makes out closing lineup very small. Hayward made such a difference when healthy not just because he was so good offensively, but also because rolling out those 3 6'7"-6'8" guys who could defend 2-4 and attack off the dribble caused mismatches that Jrue will not, and added switchability on D that Jrue may not.
Jrue to me makes the most sense if the plan is to move Kemba as well. I don't see that happening though.